Sodium Hydroxide → HCID 19907834, compound

Participants

Reaction Conditions

Reaction Steps

Petroselinyl alcohol (0.66 g, 2.46 mmoles, Sigma) was placed in a 10 ml 3-neck roundbottom flask equipped with a reflux condenser. Bromine (0.40 g, 2.5 mmole) was added slowly with magnetic stirring. After addition of the bromine, polyethylene glycol 300 (60 mg, Fluka) was added followed by powdered sodium hydroxide (0.250 g, 6.25 mmoles). A large exotherm was noted. The reaction was stirred vigorously with heating to maintain a temperature of 125° C. for 2.5 hours. The reaction was cooled and filtered to remove the solid sodium bromide. The filtered salts were washed with 25 ml of hexanes and the solvent removed. The crude product was kugelrohr distilled (ca. 200° C./ 0.20 torr) to yield 6-octadecyn-1-ol (0.49 g, 75% yield) as a clear colorless liquid which solidified upon standing.

Provenance & Evidence